9701/4 CHEMISTRY JUNE 02 - StudyGuide.PK

5 The common analgesic drug paracetamol has the following structure.8www.studyguide.pkForExaminer'sUseCH 3 CONHOH(a)Name the two functional groups in the paracetamol molecule.............................................................. and ........................................................... [2](b)Draw the structural formulae of the molecules or ions formed when paracetamol reactswith(i) Br 2(aq),(ii) NaOH(aq) in the cold,(iii) NaOH(aq) under reflux.[3](c) Paracetamol can be synthesised by reacting 4-aminophenol with compound X.H 2 NOH + Xparacetamol(i) Suggest a possible identity of X...................................................................................................................................(ii) What reagent would you use to convert ethanoic acid, CH 3CO 2H, into X?..................................................................................................................................[2][Total: 7]9701/4/S02

6 Methylbenzene can react with chlorine in two ways, depending on the conditions of thereaction.9www.studyguide.pkForExaminer'sUseCH 3CH 3CH 2 ClCl 2 Cl 2ClAreaction Ireaction IIB(a)State the condition needed for(i) reaction I,..................................................................................................................................(ii)reaction II...................................................................................................................................[2](b)One of the two compounds A and B reacts with NaOH(aq), but the other is inert.(i)Which one (A or B) does not react? Give a reason for your answer.....................................................................................................................................................................................................................................................................(ii)Write an equation for the reaction with NaOH(aq) that does occur.[2][Total: 4]9701/4/S02[Turn over

7 Phenylamine is an important intermediate compound for the production of dyes.10www.studyguide.pkForExaminer'sUsephenylamineNH 2(a)Phenylamine can be synthesised from benzene in two steps. Draw the structural formulaof the intermediate Y in the scheme below, and suggest reagents and conditions forsteps I and II.III—NH 2Yreagent + conditions for step I .........................................................................................reagent + conditions for step II ........................................................................................[4](b)Phenylamine is a weak base.(i) Write an equation showing phenylamine acting as a base.(ii) How would you expect its basicity to compare with that of ammonia?..................................................................................................................................(iii) Explain the reasoning for your answer in (ii).....................................................................................................................................................................................................................................................................[3]9701/4/S02

(c)11www.studyguide.pkForExaminer'sUseDyes can be made from phenylamine by first converting it into benzenediazoniumchloride, and then coupling this with a phenol.IIINH 2 N + 2 Cl –IV+ a phenoldye(i) State the reagents and condition needed for step III...................................................................................................................................(ii) What reagent is the phenol dissolved in for step IV to be effective?..................................................................................................................................(iii) Suggest the structural formula of the dye formed when benzenediazoniumchloride is coupled with 2-methylphenol.[4][Total: 11]9701/4/S02

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